In 1858, three whalers—William Swift, Thomas Nye, and Eben Perry—were returning to New Bedford after an expedition. After getting caught in a storm, the men spent the night on the island with Otis Slocum, who owned the island at the time. The men offered Slocum payment for his hospitality. When he refused, they instead asked Slocum to name a price for the Island—he pegged it at $50. Swift, Nye, and Perry purchased the island.
When whaling was big business in the nearby port of New Bedford, the island’s pilots were famous for the skills and experience needed to guide the vessels in and out of New Bedford harbor. Many pilots made their homes on the island and would stand atop Lookout Hill with spyglasses waiting for the whalers to come into sight. According to an 1852 history of the island compiled by a former teacher at the island’s school, Louise T. Haskell, the pilots were still very active on the island as late as 1903.
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